Acetic Acid → HCID 53822612, Verbindung

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Reaktionsgleichung

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([C:26]4[N:30]([CH3:31])[C:29]([CH:32]=O)=[CH:28][N:27]=4)[CH:24]=3)[N:19]=[CH:18][N:17]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.[NH:38]1[CH2:45][CH2:44][CH2:43][C@H:39]1[C:40]([NH2:42])=[O:41].C(O[BH3-])(=O)C.[Na+]>ClCCl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([C:26]4[N:30]([CH3:31])[C:29]([CH2:32][N:38]5[CH2:45][CH2:44][CH2:43][C@H:39]5[C:40]([NH2:42])=[O:41])=[CH:28][N:27]=4)[CH:24]=3)[N:19]=[CH:18][N:17]=2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 20 °C

Versuchsvorschrift

2-(4-(4-Benzyloxy-phenylamino)-quinazolin-6-yl)-3-methyl-3H-imidazole-4-carbaldehyde was dissolved in dichloromethane (5 ml) containing glacial acetic acid (0.03 ml). L-prolinamide (0.028 g) was added and the mixture stirred at 20° C. for 0.75 hours. Sodium acetoxyborohydride (0.08 g) was added and the reaction stirred at 20° C. for 18 hours. The mixture was partitioned between 2N sodium carbonate and ethyl acetate, the organic phase was dried over magnesium sulphate and concentrated in vacuo. Chromatography on silica gave the title compound (0.008 g) as a yellow solid; tlc (SiO2, CH2Cl2:EtOH:NH3, 100:8:1) Rf 0.18; m/z (M+1)30 534.

Aufarbeitung

stirringthe reaction stirred at 20° C. for 18 hours
customThe mixture was partitioned between 2N sodium carbonate and ethyl acetate
dry with materialthe organic phase was dried over magnesium sulphate
concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-dffb2dca9a4b403ebef0f4bda025b15f
Quelldatensatz: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06391874B1

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